Says the guy from Toronto. Dude, I am not trying to put down your city, its a great city, one of the best to live in, and its got a great skyline, that you should be proud of. But its not on Chicago's level, but it is in the top 10. I can send you links from sources proving what I am saying.

I agree 1000% with this. In North America, it's probably 4 or 5 based on all the traditional variables.

I live in Chicago, but I've visited Toronto a few times and can tell you that it is easily on the same level. Have you seen how much construction there is? It's not exactly on par just yet, because it is missing a few much needed super falls, but it is definitely on the same level. The only problem with Toronto is that it's not photogenic. Chicago has a river that runs through downtown and the buildings are built along the lakeshore, which make the typical tourist shots Chicago's best angles. Having been to Toronto's islands, I can tell you that the typical tourist shot does not even capture a quarter of Toronto's skyline.

As for placing Panama above Toronto, I'll let you be the judge of that:

I don't see why Panama City's skyline being better than Toronto's is so ludicruous. Also it's worth pointing out your "zooming in" accidently missed out on one of Panama City's biggest zone of skyscrapers (Costa del Este) and cropped off half of the ones on Avenida Balboa. I have been to New York (3 days), Chicago (2 days), Toronto (1 day), and Panama City (a lot). I found New York's to be the most amazing I've ever seen during night and liked Chicago's skyline better in the day. It looked orderly, well-structured and beautiful. Toronto's had great height and density but after having visited New York City, it didn't have a pow-factor. Sure I probably gave Panama one or two bonus points for being my home country but I don't feel I cheated Toronto out of the top 3 spot by any means. In fact, I was torn about giving Seattle #4 since that backdrop is just to die for.

PS-Boosterism is the worst way to prop up your city. People here have seen pictures of all major skylines and some have traveled to most major skylines and we can see right through it. As the other poster aptly put it, Toronto is a beautiful skyline and one of the best in North America but it's nowhere close to Chicago's and not even 10% of New York City's.

Here's some good pics of Panama City's Skyline as well:

This was the Skyline you zoomed in on. It's Punta Pacifica and in my opinion is the ugliest part of Panama City's skyline. Notice however that the backdrop of the city next to virgin rainforests adds in a great bonus in my opinion just like Mount Rainier does to Seattle or Vancouver gets from its mountains

I think one of the reason Toronto's skyline isn't as photogenic as Chicago (other than height and architecture - imo, Chicago wins) despite similar topography, Chicago's skyline is more spread out and deeply built across the lakeshore, while as you can clearly see in the Toronto aerial, Toronto's skyline is more linear and concentrated further inland which you can clearly observe when on top of CN Tower.

Chicago has a lot of historical layers you don't see in Toronto along with supertall heights and 'texture breaks' that give the skyline more depth and substance. Toronto risks becoming another Vancouver: a banal sea of concrete and glass that elicits as much enthusiasm as Panama City's sea of bland, frankly ugly, cement high rises. Architectural quality has improved noticeably in TO but not enough to offset the crystalline boxes that threaten to dominate the view from every direction.

The other thing to consider is that while Chicago is in a lull, we're seeing some of the same weak, economical glass boxes going up there so hopefully the housing market will recover before too many of those nasty rental towers start crowding out the good stuff. And considering what's already on the boards in Chicago, when that housing market returns the result will be some spectacular additions, most notably Wolf Point.

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Chicago has a lot of historical layers you don't see in Toronto along with supertall heights and 'texture breaks' that give the skyline more depth and substance. Toronto risks becoming another Vancouver: a banal sea of concrete and glass that elicits as much enthusiasm as Panama City's sea of bland, frankly ugly, cement high rises. Architectural quality has improved noticeably in TO but not enough to offset the crystalline boxes that threaten to dominate the view from every direction.

The other thing to consider is that while Chicago is in a lull, we're seeing some of the same weak, economical glass boxes going up there so hopefully the housing market will recover before too many of those nasty rental towers start crowding out the good stuff. And considering what's already on the boards in Chicago, when that housing market returns the result will be some spectacular additions, most notably Wolf Point.

As a Chicago resident, I wholeheartedly disagree with you. In my opinion, Chicago has way too many ugly buildings downtown. Just because they're older, it doesn't make them nicer than Toronto's. Also, Toronto has a much more simplistic look with clean solid lines, and I don't recall seeing a single major dilapidated building downtown. Have you been to downtown Chicago? I live in Hyde Park, and my friend lives on Montrose, so we tend to meet up in downtown quite often. I can assure you that the quality of architecture is not all that great other than the few standout high-rises. It's kind of sad to see the city in such despair, but it is obviously a result of downtown's population having decreased by almost 30% since the 60s while Toronto's, which was a fraction of Chicago's back then, is almost the exact same size now With that said, I'd still put Chicago above Toronto because we've been lucky enough to have a few gems built here, specifically, the supertalls. Other things that Chicago has over Toronto are the river and Millennium Park

Lastly, I've stayed in Panama for a few days, and whoever puts it on par with Toronto is EXTREMELY biased. The skyline is much smaller than Toronto's, the architecture is complete garbage, even for a brutalist lover like myself, and their tallest building would be completely lost even in Toronto's "Uptown" (I believe it was called Yorkville, but I may be wrong?) cluster

"EXTREMELY" biased is the person who won't let go of the stupid idea that Toronto is anywhere close to Chicago in terms of skyline. I'm pretty sure everyone here disagrees with you, every skyline ranking disagrees with you, every bit of evidence you give is just opinion based on the fact that you live in a city you obviously despise. I'd wager to say that you are just incredibly jealous of Chicago and feel the need to start a stupid discussion over it to overcome your petty inferiority complex. Everyone here is willing to acknowledge that Toronto's skyline is one of the best in North America BUT no one is willing to say it's better than Chicago's. Yet you continue to go down this endeavor, pissing off every forumer you meet and actually ruining our perceptions of Toronto in the process. Your boosterism isn't working, so cut it out!

"EXTREMELY" biased is the person who won't let go of the stupid idea that Toronto is anywhere close to Chicago in terms of skyline. I'm pretty sure everyone here disagrees with you, every skyline ranking disagrees with you, every bit of evidence you give is just opinion based on the fact that you live in a city you obviously despise. I'd wager to say that you are just incredibly jealous of Chicago and feel the need to start a stupid discussion over it to overcome your petty inferiority complex. Everyone here is willing to acknowledge that Toronto's skyline is one of the best in North America BUT no one is willing to say it's better than Chicago's. Yet you continue to go down this endeavor, pissing off every forumer you meet and actually ruining our perceptions of Toronto in the process. Your boosterism isn't working, so cut it out!

I absolutely LOVE Chicago, but unlike you, I'm all for acknowledging my city's weaknesses to give room for improvement. I guarantee that anybody that actually lives in Chicago, and isn't just a tourist there will vouch for everything I've said thus far. Please don't act like you, as a tourist, have superior knowledge of Chicago than I, a citizen. Not a single time have I said that Toronto's skyline is better than Chicago's either; I think you're just upset cause it is universally accepted that Panama doesn't even crack North America's top 10, let alone the top 5. In my opinion, Honolulu's skyline is a lot nicer than Panama's, and that doesn't even make the top 10 on most lists.

P.S. Don't lunge out and call me biased when I have continuously stated that Chicago is better than Toronto in a lot of ways. I'm just being realistic and acknowledging that Toronto has surpassed Chicago in a lot of ways, and that actually makes me sad. Especially when I see how vibrant Chicago was in movies like Ferris Bueller's Day Off. I wasn't born when that movie came out, so all I've come to see is a continuous decline, and I absolutely despise the city's administration and hold them 100% accountable for all of this. If you think I hate Chicago, you are DEAD wrong, as I have and will continuously state, I think it has North America's best skyline. Go back a few pages, I even ranked it on top of NY. In my opinion, you are just upset because your bias towards your hometown is so farfetched it makes most people here laugh. Putting Panama 3rd in North America? You think Panama has a nicer skyline than Houston, LA, Miami, Seattle? LOL...

Especially when I see how vibrant Chicago was in movies like Ferris Bueller's Day Off. I wasn't born when that movie came out, so all I've come to see is a continuous decline...

Really? In the mid-1980s Chicago was much more rundown and stagnant than it is today. While there's the odd neighborhood that has continued to go downhill, most of the city is far healthier than it was 25 years ago. When Ferris Bueller was filmed, everything south and west of the Loop was a sea of abandoned lots and empty warehouses, not the thriving neighborhoods they are today. River North was dominated by Cabrini Green, now it's dominated by the sea of (admittedly ugly but economically vital) highrises that has sprung up there. Yes, the population has still dipped slightly from the mid 1980s, but economically Chicago is a lot better off, and more sustainable, than in 1986. Back then, stable neighborhoods were pretty much the North Side and that's it. Now, the Milwaukee Avenue corridor is booming and pushing out into other neighborhoods, Hispanics have revitalized Pilsen and much of the Southwest Side, and even the Hyde Park area is seeing gentrification push out into the urban wilderness. Like any big city, Chicago has had ups and downs, but it hasn't seen the continuing collapse that was threatening to happen in the 1970s and early 1980s.

Really? In the mid-1980s Chicago was much more rundown and stagnant than it is today. While there's the odd neighborhood that has continued to go downhill, most of the city is far healthier than it was 25 years ago. When Ferris Bueller was filmed, everything south and west of the Loop was a sea of abandoned lots and empty warehouses, not the thriving neighborhoods they are today. River North was dominated by Cabrini Green, now it's dominated by the sea of (admittedly ugly but economically vital) highrises that has sprung up there. Yes, the population has still dipped slightly from the mid 1980s, but economically Chicago is a lot better off, and more sustainable, than in 1986. Back then, stable neighborhoods were pretty much the North Side and that's it. Now, the Milwaukee Avenue corridor is booming and pushing out into other neighborhoods, Hispanics have revitalized Pilsen and much of the Southwest Side, and even the Hyde Park area is seeing gentrification push out into the urban wilderness. Like any big city, Chicago has had ups and downs, but it hasn't seen the continuing collapse that was threatening to happen in the 1970s and early 1980s.

Yes, Cabrini Green its still fresh in the mindsets of most people, but to say that more of Chicago was abandoned in 1980 than today is ludicrous.

Chicago's population in 1980: 3,005,072
Chicago's population in 2010: 2,695,598

Losing 10% of its population is not a slight dip by any means. I wish I were as optimistic as you, but if you go to the Chicago forum, you will see that other users, such as chicagogeorge are also willing to speak the truth.

Since when has absolute population change been a good indicator of a city's economic health? Not to mention that over two-thirds of that drop you mention took place in the 1980s. The past twenty years has seen the population stabilize, and Cook County is gaining people once more, meaning the city most likely is as well. Sure, I'm optimistic, but what makes pessimism any more of the truth? Chicago is a hell of a lot tougher and durable than either you or George give the city credit for. The city's simply too important to the country, and world economy, to fade away, and there's a reason I'm looking forward to living in Chicago instead of a New York or San Francisco.

People should be allowed to post their opinions without being insulted or called biased. If someone thinks Pittsburgh is the best in north America that doesn't mean they're a moron or have a Pittsburgh bias. That's my 2 cents.

Since when has absolute population change been a good indicator of a city's economic health? Not to mention that over two-thirds of that drop you mention took place in the 1980s. The past twenty years has seen the population stabilize, and Cook County is gaining people once more, meaning the city most likely is as well. Sure, I'm optimistic, but what makes pessimism any more of the truth? Chicago is a hell of a lot tougher and durable than either you or George give the city credit for. The city's simply too important to the country, and world economy, to fade away, and there's a reason I'm looking forward to living in Chicago instead of a New York or San Francisco.

Funny; that's what was said about Detroit. How about we try something different instead of blindfolding ourselves and hoping for the best this time around?

Funny; that's what was said about Detroit. How about we try something different instead of blindfolding ourselves and hoping for the best this time around?

Funny, I actually am planning to do something about it instead of taking the easy approach and cutting and running to the suburbs. Soon as school is done, I plan to be in Chicago, spending my money in the city limits, and I plan to raise my children in the city as well. If only more people were willing to do so, but I believe my generation will be the one that revitalizes our cities.

Funny, I actually am planning to do something about it instead of taking the easy approach and cutting and running to the suburbs. Soon as school is done, I plan to be in Chicago, spending my money in the city limits, and I plan to raise my children in the city as well. If only more people were willing to do so...

Dallas might be my favorite of the 1980s oil boom skylines, as there are some interesting color and texture choices in the Dallas skyline. The green of the Renaissance Tower and the curved top of the Comerica Bank Building come to mind.